South Eastern Ontario is just too beautiful in the wintertime to stay indoors.

While it can be tempting to hibernate all season, this list of our top picks for events will have you living the snowy season to the fullest. Keep this page bookmarked to refer back to as we add to our listings. For Holiday related events, check out our blog below.

When: December 3rd to 17th, 2022

Get your finger on the pulse of upcoming musicians that are just moments away from their big break. For the entire month of December you can enjoy local music in the stunning downtown Kingston, right next to city hall. Every weekend local musicians will be sharing their talents, while you warm up with hot apple cider beside an outdoor firepit. Keep an eye out as the talent lineup will be listed soon!

When: February 2023

Each year Kingston hosts a culinary experience that can’t be beaten! Enjoy delicious food at an affordable price from local eateries including Atomica, AquaTerra, Chez Piggy, Secret Garden Inn and many more. 

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When: December 11th to 18th, 2022

Having been on hiatus since 2019, the World Junior A Challenge will be representing Hockey Canada and the Canadian Junior Hockey League, Hockey Eastern Ontario and NHL Central Scouting with a series of games where the top four teams can advance for their chance to win the World Junior A gold medal on December 18th!

When: Various Dates in December 2022

Check out live music happening and special events at The Cove. Featuring Krief, Angelique Francis, Young Petty Stones, and more!

When: January 28th to 29th, 2023

For almost two decades the community has come together to celebrate the cold weather with the Skate the Lake community event! Skaters can take part in 5K, 10K, 25K and 50K races and show off their skills in Portland this January, so register now!

When: February 2023

Just because the holidays are over in January, doesn’t mean you don’t have plenty of fun to look forward to during the cold winter months of the new year. Join your pals in Kemptville for the annual Winter Carnival! Enjoy hot chocolate, skating, horse drawn sleigh rides, plenty of races and fun to be had for all ages, and its free to enter!

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When: Saturday, December 3rd

Enjoy an evening of wine, food, and live music with a tasting led by Vintner, Sherry Karlo. Tantalize your senses with a three-flight wine tasting, perfectly paired to delicious home-made cuisine. View their website for more upcoming events.

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When: February 19th, 2023

Set the stage for entertainment at the Brockville Arts Centre this winter! The new year welcomes multi-award-winning folk-pop singer, songwriter and actress, Jann Arden to the Brockville Arts Centre. Jan has produced ten studio albums with 17 top singles and has toured with the ever-talented Michael Buble! Get into the music in February by grabbing a ticket for this spectacular concert.

When: February 23rd, 2023

Whether you are planning your nuptials or you are dreaming of the future, you should definitely check out the Brockville Wedding Show! Enjoy a stunning fashion show, live music and plenty of raffles while you meet with local vendors who offer unique and special wedding products and services.

Get into the holiday spirit with 25 Of The Best Ontario Holiday Markets & Experiences

Photo provided by @visitkingstonca